4-(2-硝基苯氧基)苯甲醛 | 172932-06-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(2-硝基苯氧基)苯甲醛
• 英文名称: 4-(2-nitrophenoxy)benzaldehyde
• 英文别名: 4-(2-nitro-phenoxy)-benzaldehyde；4-(2-Nitro-phenoxy)-benzaldehyd
• CAS: 172932-06-8
• 化学式: C₁₃H₉NO₄
• mdl: MFCD13207024
• 分子量: 243.219
• InChiKey: DQICVGKJZQGBOG-UHFFFAOYSA-N

物化性质

• 熔点：
  84-85 °C
• 沸点：
  380.8±27.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-硝基苯氧基)苯甲醛 在 吡啶 、 三乙烯二胺 、 sodium tetrahydroborate 、 铁粉 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.99h， 生成 (E)-methyl 2-methyl-3-(4-(2-(3-phenylthioureido)phenoxy)phenyl)acrylate
  参考文献：
  名称：

  Synthesis and evaluation of new diaryl ether and quinoline hybrids as potential antiplasmodial and antimicrobial agents

  摘要：

  Synthesis and bioevaluation of new diaryl ether hybridized quinoline derivatives as antiplasmodial, antibacterial and antifungal agents is reported. It was encouraging to discover that several compounds displayed 2-3 folds better efficacy than chloroquine in chloroquine-resistant K1 strain of Plasmodium falciparum. Further, a few members of the library displayed good antibacterial efficacy against gram positive strains of bacteria but none of the compounds displayed any significant antifungal activity. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.02.044
• 作为产物：
  描述：

  二苯醚 在 盐酸 、 三氯化铝 、 水 、 硝酸 、 苯 作用下， 生成 4-(2-硝基苯氧基)苯甲醛
  参考文献：
  名称：

  Slotta; Soremba, Chemische Berichte, 1935, vol. 68, p. 2059,2063

  摘要：

  DOI：

文献信息

• Importance of the Proximity and Orientation of Ligand-Linkage to the Design of Cinnamate-GW9662 Hybrid Compounds as Covalent PPARγ Agonists
  作者：Yuki Utsugi、Hirona Kobuchi、Yukio Kawamura、Ahmed Salahelden Aboelhamd Atito、Masaya Nagao、Hiroko Isoda、Yusaku Miyamae

  DOI：10.3390/molecules24102019

  日期：——

  Covalent agonists of PPARγ cause unique receptor conformational changes and behave as selective PPARγ modulators, whereas there are few covalent agonists other than endogenous unsaturated fatty acids metabolites. Previously, we established a cell-based strategy to identify new PPARγ ligands and synthesized a new-type of covalent agonist that possesses the hybrid structure of a plant-derived cinnamic acid derivative and GW9662, a covalent antagonist. Herein, we report six analogues that differ in how the two fragments are linked together. Compounds with a simplified linker showed potent agonistic activity with improved EC50 values (less than 5 nM), indicating that close proximity between the two fragments improves binding affinity. When the position of cinnamic acid moiety was placed at 4′ carbon of aniline ring, PPARγ agonist activity was completely abolished. Docking studies suggested that the activation profile likely depends on interaction with the cavity around helix 3, β-sheet, and Ω-loop region in the ligand-binding domain. Furthermore, a cell-based assay revealed that agonist-type compounds activate PPARγ transcription in a manner dependent on covalent linkage with the Cys285 residue leading to prolonged transactivation. This activation feature reflects pharmacological benefits of covalent drugs, suggesting that these hybrid compounds may serve as potential leads for a new-class of covalent PPARγ ligands.

  PPARγ的共价激动剂引起独特的受体构象变化，并表现为选择性PPARγ调节剂，而除内源性不饱和脂肪酸代谢产物外，几乎没有其他共价激动剂。我们先前建立了一种基于细胞的策略来识别新的PPARγ配体，并合成了一种新型的共价激动剂，其具有植物衍生的肉桂酸衍生物和GW9662（一种共价拮抗剂）的混合结构。在这里，我们报告了六种在两个片段如何连接在一起上有所不同的类似物。具有简化连接剂的化合物显示出强大的激动活性，具有改善的EC50值（小于5 nM），表明两个片段之间的密切接近改善了结合亲和力。当肉桂酸部分的位置放置在苯胺环的4'碳上时，PPARγ激动剂活性完全被废除。对接研究表明，激活特性可能取决于与配体结合结构域中螺旋3、β-片和Ω-环区域周围的空腔的相互作用。此外，基于细胞的实验揭示出激动剂型化合物以依赖于与Cys285残基的共价连接导致持续的转录激活的方式激活PPARγ转录。这种激活特性反映了共价药物的药理学益处，表明这些混合物可能作为新型共价PPARγ配体的潜在引物。
• Treatment of Alzheimer's disease employing inhibitors of cathepsin D
  申请人：ELI LILLY AND COMPANY

  公开号：EP0677517A1

  公开（公告）日：1995-10-18

  This invention provides novel benzylidene rhodanines of the formula wherein nis 0, 1, 2, 3, or 4; qis 0, 1, 2, 3, or 4; Ais -O, -NH-, or -S(O)m-;    where m is 0, 1, or 2; R¹is hydrogen, C₁-C₆ alkyl, di(C₁-C₆ alkyl)amino-, amino, (C₁-C₆ alkyl)amino-, cyano(C₁-C₆ alkyl)-, or carboxy(C₁-C₆ alkylidenyl)-; Ris phenyl, oxazolyl, benzophenonyl, or naphthyl optionally substituted with one or more substituents, which are useful as agents in treating or preventing conditions associated with β-amyloid peptide. This invention further provides methods of treating or preventing Alzheimer's Disease which comprises administering to a mammal in need thereof an effective amount of one or more of the benzylidene rhodanines of the present invention. This invention also provides methods for reducing blood glucose concentrations which comprises administering to a mammal in need thereof an effective amount of one or more of the benzylidene rhodanines of the present invention.

  本发明提供了式如下的新型亚苄基罗丹宁 式中 n为0、1、2、3或4； q为0、1、2、3或4； A是-O、-NH-或-S(O)m-； 其中 m 为 0、1 或 2； R¹是氢、C₁-C₆烷基、二(C₁-C₆烷基)氨基、氨基、(C₁-C₆烷基)氨基、氰基(C₁-C₆烷基)-或羧基(C₁-C₆亚烷基)-； 里氏苯基、恶唑基、二苯甲酮基或任选被一个或多个取代基取代的萘基，可用作治疗或预防与 β 淀粉样肽相关的疾病的药物。本发明进一步提供了治疗或预防阿尔茨海默病的方法，其中包括向有需要的哺乳动物施用有效量的一种或多种本发明的亚苄基罗丹宁。本发明还提供了降低血糖浓度的方法，其中包括向有需要的哺乳动物施用有效量的一种或多种本发明的亚苄基罗丹宁。
• Inhibitors of HCV NS5B polymerase. Part 1: Evaluation of the southern region of (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid
  作者：Jeffrey A. Pfefferkorn、Meredith L. Greene、Richard A. Nugent、Rebecca J. Gross、Mark A. Mitchell、Barry C. Finzel、Melissa S. Harris、Peter A. Wells、John A. Shelly、Robert A. Anstadt、Robert E. Kilkuskie、Laurice A. Kopta、Francis J. Schwende

  DOI：10.1016/j.bmcl.2005.03.066

  日期：2005.5

  A novel series of nonnucleoside HCV NS5B polymerase inhibitors were prepared from (2Z)-2-(benzoylamino)-3-(5-phenyl-2-furyl)acrylic acid, a high throughput screening lead. SAR studies combined with structure based drug design focusing on the southern heterobiaryl region of the template led to the synthesis of several potent and orally bioavailable lead compounds. X-ray crystallography studies were also performed to understand the interaction of these inhibitors with HCV NS5B polymerase.
• STUDIES IN THE DIPHENYL ETHER SERIES. III. DERIVATIVES OF THE LOCAL ANESTHETIC TYPE
  作者：C. M. Suter、Elmer. Oberg

  DOI：10.1021/ja01355a060

  日期：1931.4
• Horii, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1938, vol. 58, p. 926,927; dtsch. Ref. S. 295
  作者：Horii

  DOI：——

  日期：——